EP0719772B1 - Derive d'imidazolidinone et procede pour sa production - Google Patents

Derive d'imidazolidinone et procede pour sa production Download PDF

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Publication number
EP0719772B1
EP0719772B1 EP94926387A EP94926387A EP0719772B1 EP 0719772 B1 EP0719772 B1 EP 0719772B1 EP 94926387 A EP94926387 A EP 94926387A EP 94926387 A EP94926387 A EP 94926387A EP 0719772 B1 EP0719772 B1 EP 0719772B1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
groups
general formula
imidazolidinone
addition salts
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP94926387A
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German (de)
English (en)
Other versions
EP0719772A1 (fr
EP0719772A4 (fr
Inventor
Yasuo Takano
Kei Okazaki
Takashi 3-6-2-304 Sakurada Hirayama
Tsuyoshi 5932 Aza-Unoki Tomonuma Anraku
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Kyorin Pharmaceutical Co Ltd
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Kyorin Pharmaceutical Co Ltd
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Application filed by Kyorin Pharmaceutical Co Ltd filed Critical Kyorin Pharmaceutical Co Ltd
Publication of EP0719772A1 publication Critical patent/EP0719772A1/fr
Publication of EP0719772A4 publication Critical patent/EP0719772A4/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Definitions

  • (S)-1-phenylmethyl-3-aminopiperidine was synthesized similarly to referential examples 6 and 7, after (s)-ethyl nipecotate from ( ⁇ )-ethyl nipecotate was synthesized by the method described in Recueil. Travl. chim. Pays-Bas, 70 , 899 (1951).
  • mice In the retention trial, mouse was placed again in the light room and the time until they moved into the dark room was measured for at maximum 300 seconds as a reaction latency; for mouse exhibited longer latency than those, the time was made to be 300 seconds.
  • the induction of amnesia was performed by fixing a mouse at prone position without anesthetization at 20 minutes before learning acquisition trial and injecting pirenzepine (10 ⁇ g/2 ⁇ l/mouse bilaterally into cerebral ventricles using a microsyringe.
  • pirenzepine 10 ⁇ g/2 ⁇ l/mouse bilaterally into cerebral ventricles using a microsyringe.
  • a group not to administered with pirenzepine before acquisition trial was also provided.
  • the mice were made to be 12 to 21 animals per group and the testing compound was administered orally at 30 or 60 minutes before acquisition trial.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Hospice & Palliative Care (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Psychiatry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (8)

  1. Dérivé d'imidazolidinone optiquement actif représenté par la formule générale (1) :
    Figure 00540001
    (dans laquelle R et R1 sont identiques ou différents et représentent des atomes d'hydrogène, des atomes d'halogènes, des groupements alkyles inférieurs possédant de 1 à 6 atomes de carbone et pouvant être substitués par des atomes d'halogènes, des groupements alcoxy inférieurs possédant de 1 à 4 atomes de carbone, des groupements alkylthio inférieurs possédant de 1 à 6 atomes de carbone, des groupements alcoxycarbonyles possédant 1 ou 2 atomes de carbone au niveau du groupement alcoxy, des groupes nitro, des groupes amino pouvant être substitués par des groupements acétyle ou par un ou deux groupements alkyles inférieurs possédant de 1 à 6 atomes de carbone, ou des groupe cyano, et où n va de 1 à 4), ou leur sels d'addition acide.
  2. Composé ou sel d'addition acide d'un composé selon la revendication 1, caractérisé en ce que R est un atome d'hydrogène, en ce que R1 est choisi indifféremment parmi un atome d'halogène, un groupement alkyle inférieur possédant de 1 à 6 atomes de carbone et pouvant être substitué par un atome d'halogène, ou un groupement alcoxy inférieur possédant de 1 à 4 atomes de carbone, et en ce que n est 1 dans la formule générale (1).
  3. Composé ou sel d'addition acide d'un composé selon la revendication 1, caractérisé en ce que R1 est atome d'halogène, en ce que R est choisi indifféremment parmi un atome d'halogène, un groupement alkyle inférieur possédant de 1 à 6 atomes de carbone et pouvant être substitué par un atome d'halogène et un groupement alcoxy possédant de 1 à 4 atomes de carbone, et en ce que n est 1 dans la formule générale (1).
  4. Composé ou sel d'addition acide d'un composé selon la revendication 1, caractérisé en ce que le dit composé est la (R)-1-(4-fluorophényl)-3-[3-1-(phénylméthylpipéridyl)]-2-imidazolidinone.
  5. Composé ou sel d'addition acide d'un composé selon la revendication 1, caractérisé en ce que ledit composé est la (R)-1-(3-fluorophényl)-3-[3-(1-(phénylméthylpipéridyl)]-2-imidazolidinone.
  6. Composé ou sel d'addition acide d'un composé selon la revendication 1, caractérisé en ce que ledit composé est la (R)-1-(4-trifluorométhylphényl)-3-[3-(1-(phénylméthylpipéridyl)]-2-imidazolidinone.
  7. Composé ou sel d'addition acide d'un composé selon la revendication 1, caractérisé en ce que ledit composé est la (R)-1-(3-trifluorométhylphényl)-3-[3-(1-(phénylméthylpipéridyl)]-2-imidazolidinone.
  8. Médicament contre la démence, caractérisé en ce qu'il contient comme composant(s) efficace(s) un ou plusieurs dérivé(s) d'imidazolidinone représenté(s) par la formule générale :
    Figure 00550001
    (dans laquelle R et R1 sont identiques ou différents et représentent des atomes d'hydrogène, des atomes d'halogènes, des groupements alkyles inférieurs possédant de 1 à 6 atomes de carbone et pouvant être substitués par des atomes d'halogènes, des groupements alcoxy inférieurs possédant de 1 à 4 atomes de carbone, des groupements alkylthio inférieurs possédant de 1 à 6 atomes de carbone, des groupements alcoxycarbonyles possédant 1 ou 2 atomes de carbone au niveau du groupement alcoxy, des groupes nitro, des groupes amino pouvant être substitués par des groupements acétyle ou par un ou deux groupements alkyles inférieurs possédant de 1 à 6 atomes de carbone, ou des groupe cyano, et où n va de 1 à 4), ou leur sels d'addition acide.
EP94926387A 1993-09-17 1994-09-12 Derive d'imidazolidinone et procede pour sa production Expired - Lifetime EP0719772B1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
JP25498393 1993-09-17
JP254983/93 1993-09-17
JP25498393 1993-09-17
JP242264/94 1994-09-09
JP24226494A JP3916093B2 (ja) 1993-09-17 1994-09-09 光学活性イミダゾリジノン誘導体とその製造方法
JP24226494 1994-09-09
PCT/JP1994/001505 WO1995007905A1 (fr) 1993-09-17 1994-09-12 Derive d'imidazolidinone et procede pour sa production

Publications (3)

Publication Number Publication Date
EP0719772A1 EP0719772A1 (fr) 1996-07-03
EP0719772A4 EP0719772A4 (fr) 1996-09-04
EP0719772B1 true EP0719772B1 (fr) 2000-07-12

Family

ID=26535688

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94926387A Expired - Lifetime EP0719772B1 (fr) 1993-09-17 1994-09-12 Derive d'imidazolidinone et procede pour sa production

Country Status (15)

Country Link
US (1) US5726188A (fr)
EP (1) EP0719772B1 (fr)
JP (1) JP3916093B2 (fr)
KR (1) KR100323930B1 (fr)
CN (1) CN1041088C (fr)
AT (1) ATE194611T1 (fr)
AU (1) AU679259B2 (fr)
CA (1) CA2172162C (fr)
DE (1) DE69425266T2 (fr)
DK (1) DK0719772T3 (fr)
ES (1) ES2149281T3 (fr)
GR (1) GR3034499T3 (fr)
HU (1) HU217668B (fr)
PT (1) PT719772E (fr)
WO (1) WO1995007905A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09504272A (ja) * 1993-09-15 1997-04-28 メルク シヤープ エンド ドーム リミテツド ドーパミンアンタゴニストとしてのイミダゾロン及びオキサゾロン誘導体
US6159990A (en) * 1997-06-18 2000-12-12 Synaptic Pharmaceutical Corporation Oxazolidinones as α1A receptor antagonists
US6316623B1 (en) * 1998-08-21 2001-11-13 Isis Pharmaceuticals, Inc. Ethylenediamine compound libraries
BR0213611A (pt) * 2001-10-02 2005-12-20 Acadia Pharm Inc Composto, composição farmacêutica, seus usos, método para aumentar a atividade de um receptor colinérgico, métodos para tratamento ou prevenção de distúrbio mental, dor, pressão intraocular aumentada e progressão ou formação de placas amilóides
US6951849B2 (en) * 2001-10-02 2005-10-04 Acadia Pharmaceuticals Inc. Benzimidazolidinone derivatives as muscarinic agents
WO2007036718A2 (fr) * 2005-09-30 2007-04-05 Glaxo Group Limited Composes exerçant une activite au niveau du recepteur m1 et leurs utilisations en medecine
WO2007036711A1 (fr) * 2005-09-30 2007-04-05 Glaxo Group Limited Benzimidazolones exerçant une activite au niveau du recepteur m1
US8283364B2 (en) * 2005-09-30 2012-10-09 Glaxo Group Limited Compounds which have activity at M1 receptor and their uses in medicine
EP2123769B1 (fr) 2007-02-19 2016-05-18 Kaneka Corporation Procédé de fabrication de 3-aminopipéridine optiquement active ou d'un sel de celle-ci
EP2457899A4 (fr) * 2009-07-21 2015-06-03 Sumitomo Chemical Co Procédé pour la production de nipecotamide optiquement actif

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US459757A (en) * 1891-09-22 Electric-arc lamp
US3196152A (en) * 1965-07-20 Phenyl and alkyleneamino substituted imidazolidinones and salts thereof
US3355457A (en) * 1965-05-21 1967-11-28 American Cyanamid Co Substituted 2-imidazolinones
US3459757A (en) * 1965-10-22 1969-08-05 American Cyanamid Co Imidazolidines
US4011238A (en) * 1972-07-26 1977-03-08 Gruppo Lepetit S.P.A. 2-imidazolidione derivatives
GB9106571D0 (en) * 1991-03-27 1991-05-15 Erba Carlo Spa Derivatives of substituted imidazol-2-one and process for their preparation
US5300515A (en) * 1991-01-31 1994-04-05 Kyorin Pharmaceutical Co., Ltd. Carbamic acid derivatives and method for preparing the same
JPH09504272A (ja) * 1993-09-15 1997-04-28 メルク シヤープ エンド ドーム リミテツド ドーパミンアンタゴニストとしてのイミダゾロン及びオキサゾロン誘導体

Also Published As

Publication number Publication date
CA2172162A1 (fr) 1995-03-23
AU7624394A (en) 1995-04-03
WO1995007905A1 (fr) 1995-03-23
CA2172162C (fr) 2005-04-19
DE69425266D1 (de) 2000-08-17
DK0719772T3 (da) 2000-11-06
KR960704878A (ko) 1996-10-09
CN1041088C (zh) 1998-12-09
DE69425266T2 (de) 2001-02-22
AU679259B2 (en) 1997-06-26
CN1135216A (zh) 1996-11-06
EP0719772A1 (fr) 1996-07-03
ES2149281T3 (es) 2000-11-01
ATE194611T1 (de) 2000-07-15
JP3916093B2 (ja) 2007-05-16
HU9600622D0 (en) 1996-05-28
HUT75649A (en) 1997-05-28
JPH07133273A (ja) 1995-05-23
EP0719772A4 (fr) 1996-09-04
PT719772E (pt) 2000-11-30
KR100323930B1 (ko) 2004-05-06
HU217668B (hu) 2000-03-28
GR3034499T3 (en) 2000-12-29
US5726188A (en) 1998-03-10

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